Staff Software Engineer, AI Developer Tooling

Details

Sentry helps developers fix errors and performance issues before users notice. Trusted by more than 200,000 organizations, Sentry is building an AI-native future for software development.

This role sits within Platform Engineering and owns the AI-assisted coding domain across Sentry. You will focus on how AI coding agents participate in the software development lifecycle, making internal systems accessible through APIs and building connections that allow tools such as Claude Code to operate end-to-end.

You will work across infrastructure, backend systems, and developer tooling, with a focus on context engineering, harness engineering, agent permissions, state management, testing, logging, retries, checkpoints, guardrails, and evaluations. You will collaborate with the developer infrastructure team and product teams across Sentry to improve how engineers ship software.

Responsibilities

• Audit Sentry's internal developer systems and make them API-ready for AI agents.
• Prioritize and drive work to expose internal systems programmatically and build connections that allow agents to operate on them end-to-end.
• Build harness tooling, context systems, and feedback loops that help agents generate high-quality, repository-aware pull requests.
• Develop automated pre-review checks and pull request quality measurement tailored to Sentry's codebase.
• Automate high-volume, low-priority engineering work, including security dependency upgrades, minor bug fixes, and routine maintenance.
• Design and build internal tools such as productivity dashboards, AI-assisted issue triage, CI/CD optimizations, and developer productivity tooling.
• Identify and remove organizational friction using data and direct observation.
• Recommend solutions to senior leadership and build cross-team support for technical and organizational changes.

Requirements

• 10+ years of software engineering experience.
• Experience building tools or workflows that improve how developers or AI agents work. Relevant backgrounds may include CI/CD, developer infrastructure, AI harness tooling, AI-first coding workflows, or public contributions in this area.
• Strong software and system design fundamentals.
• Genuine curiosity about and hands-on experience with AI coding tools and agents. Prior machine learning experience is not required.
• Excellent written and verbal communication skills, including the ability to present to senior technical leadership.
• A track record of driving cross-team technical initiatives to completion.
• Ability to work across infrastructure, backend, and developer tooling.
• Ability to work independently in ambiguous situations, make sound technical decisions, and move between strategic and hands-on work.
• Ability to communicate clearly, influence without authority, and build cross-team buy-in.

Nice to Have

• Experience with large-scale distributed systems or monolith decomposition.
• Experience with developer experience or engineering productivity programs.
• Familiarity with code review tooling, static analysis, or automated pull request pipelines.

Benefits

• Base salary range of $240,000 to $400,000.
• Eligibility for incentive compensation, equity grants, paid time off, and group health insurance coverage.
• Estimated bonus range of $36,000 to $60,000.
• Equal employment opportunities and reasonable accommodations for candidates and employees with disabilities.